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(12) United States Patent (10) Patent No.: US 9.066,945 B2 Turberg Et Al

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(12) United States Patent (10) Patent No.: US 9.066,945 B2 Turberg Et Al USOO9066945B2 (12) United States Patent (10) Patent No.: US 9.066,945 B2 Turberg et al. (45) Date of Patent: Jun. 30, 2015 (54) ECTOPARASITICIDAL ACTIVE SUBSTANCE 2011, 0021539 A1 1/2011 Schwarz et al. COMBINATIONS 2011/O257231 A1 10/2011 Koyanagi et al. 2011/0306499 A1 12/2011 Bretschneider et al. (75) Inventors: Andreas Turberg, Haan (DE); Ulrich Görgens, Ratingen (DE); Hans-Georg FOREIGN PATENT DOCUMENTS Schwarz, Dorsten (DE); Stefan Werner, EP O382173 A2 8, 1990 Berlin (DE) EP O5395.88 A1 5, 1993 EP 2248422 A1 11 2010 (73) Assignee: Bayer Intellectual Property GmbH, JP 2007091708 4/2007 Monheim (DE) JP 2008110971 5, 2008 JP 2008133273 6, 2008 (*) Notice: Subject to any disclaimer, the term of this WO 2005035486 A1 4/2005 patent is extended or adjusted under 35 WO 2007027842 A1 3, 2007 U.S.C. 154(b) by 32 days. WO 2007043677 A1 4/2007 WO 20070487.33 A1 5/2007 (21) Appl. No.: 13/995,958 WO 2007075459 A2 7/2007 WO 2007O95229 A2 8, 2007 (22) PCT Filed: Dec. 19, 2011 WO 2007125984 A1 11, 2007 WO 2007 149134 A1 12/2007 (86). PCT No.: PCT/EP2011/073280 WO 2008104503 A1 9, 2008 WO 2008128711 A1 10, 2008 S371 (c)(1), WO 2009002809 A2 12/2008 (2), (4) Date: Feb. 17, 2014 WO 2009024541 A2 2, 2009 WO 2009060015 A1 5, 2009 (87) PCT Pub. No.: WO2012/084852 WO 2009097992 A1 8, 2009 PCT Pub. Date: Jun. 28, 2012 WO 2009 112275 A1 9, 2009 WO 2010020522 A1 2, 2010 (65) Prior Publication Data WO 2010043315 A1 4/2010 WO 2010090344 A1 8, 2010 US 2014/0179623 A1 Jun. 26, 2014 OTHER PUBLICATIONS (30) Foreign Application Priority Data Cossio-Bayugar et al., “Cytochrome P-4SO Monooxygenase Gene Dec. 21, 2010 (DE) ......................... 10 2010 O63 691 Expression Supports a Multifactorial Origin for Acaricide Resistance in Ripicephalus microplus.” Research Journal Parasitology, 2008, (51) Int. Cl. 3(2):59-66. A6 IK 45/06 (2006.01) Foil et al., “Factors that influence the prevalence of acaricide resis A 6LX3L/2197 (2006.01) tance and tick-borne diseases.” Veterinary Parasitology, 2004, AOIN 43/60 (2006.01) 125:163-181. CO7D 40/4 (2006.01) OZoe et al., “The antiparasitic isoxazoline A1443 is a potent blocker CO7D 403/04 (2006.01) of insect ligand-gated chloride channels. Biochemical and Bio CO7D 403/4 (2006.01) physical Research Communications, 2010, 391:744-749. CO7D 405/4 (2006.01) The Pesticide Manual, 14th Edition, British Crop Portection Council, (52) U.S. Cl. 2006, cover sheet, iii, and 1278-1342. CPC .............. A6 IK3I/497 (2013.01): A0IN 43/60 Rosario-Cruz et al., “Genetic basis and impact of tick acaricide (2013.01); C07D401/14 (2013.01); C07D resistance.” Frontiers in Bioscience, Jan. 1, 2009, 14:2657-2665. 403/04 (2013.01); C07D 403/14 (2013.01); C07D405/14 (2013.01); A61K 45/06 (2013.01) * cited by examiner (58) Field of Classification Search USPC ........................ 514/28, 255.05, 250:544/405 See application file for complete search history. Primary Examiner — Rei-Tsang Shiao (56) References Cited (57) ABSTRACT U.S. PATENT DOCUMENTS The present application relates to active compound combina 7,872,036 B2 1/2011 Toriyabe et al. 7,897,543 B2 3/2011 Bretschneider et al. tions of pyrazin-2-ylpyrazoles (component A) with at least 8,084,452 B2 12/2011 Jeschke et al. one further ectoparasiticide or synergists (component B), and 8, 106,212 B2 1/2012 Jeschke et al. to products comprising Such active compound combinations. 8,138,213 B2 3/2012 Mita et al. These active compound combinations are suitable for con 8,268,754 B2 9, 2012 Mita et al. 8,367,707 B2 2/2013 Goto et al. trolling animal pests in the field of Veterinary medicine. 8,513,260 B2 * 8/2013 Schwarz et al. ......... 514,255.05 8,546,577 B2 10/2013 Jeschke et al. 2010/0173948 A1 7, 2010 Lahm et al. 23 Claims, No Drawings US 9,066,945 B2 1. 2 ECTOPARASITICDAL ACTIVE SUBSTANCE alkylsulphanyl. haloalkylsulphanyl, alkylsulphinyl, COMBINATIONS haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cyano, nitro, alkylcarbonyl, alkoxycarbonyl, alkoxycarbony The present application relates to active compound com lalkyl, carboxyl, carboxamide, dialkylcarboxamide, trialkyl binations of pyrazin-2-ylpyrazoles (component A) with at silyl, amino, alkylamino, dialkylamino, alkylsulphony least one further ectoparasiticide or synergists (component lamino, dialkylsulphonylamino, formyl, —CH=NO H. B), and to products comprising Such active compound com -CH=NO-alkyl, -CH=NO-haloalkyl, -C(CH) binations. These active compound combinations are Suitable —NO H. —C(CH)—NO-alkyl, -C(CH)—NO-ha for controlling animal pests in the field of veterinary medi loalkyl; and phenyl, 2-pyridyl and 3-pyridyl which are C1G. 10 optionally Substituted by one or more halogen atoms, cyano, WO 2007/048733A describes the use of aminopyrazoles nitro, alkyl, alkoxy or haloalkyl, where vicinal alkyl, for controlling phytopathogenic harmful fungi, which in a haloalkyl, alkoxy and/or haloalkoxy groups at the phenyl general manner also includes pyrazin-2-ylpyrazoles. The substituent, 2-pyridyl substituent or 3-pyridyl substituent pyrazin-2-ylpyrazoles carry only hydrogen as Substituent in together with the carbon atoms to which they are attached the 3-position. 15 may form a five- to six-membered cyclic system which con WO 2007/027842A discloses anilinopyrazoles which may tains 0 to oxygen or nitrogenatoms, where two oxygenatoms be substituted in the 1-position of the pyrazole moiety by are not directly attached to one another, and whose alkyl 2-pyrazines. This international application relates to pharma moiety may optionally be substituted by one or more halogen ceutical applications, in particular to the treatment of diabe atoms and/or further alkyl radicals, tes; an arthropodicidal action is not described. R" represents alkyl which is optionally monosubstituted or The active compounds already known from the publica independently poly Substituted by alkoxy, haloalkoxy, alkyl tions mentioned above have disadvantages in their applica Sulphanyl, haloalkylsulphanyl, alkylsulphinyl, haloalkylsul tion; in particular, they have only unsatisfactory insecticidal phinyl, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, activity, if any. Moreover, for the known classes of active alkoxycarbonyl, hydroxyland/or cycloalkyl; alkenyl which is compounds resistance has already been observed in some 25 optionally monosubstituted or independently polysubstituted applications (Veterinary Parasitology (2004) 125, 163-181; by halogen, alkoxy, haloalkoxy, alkylsulphanyl, haloalkylsul Research Journal Parasitology (2008) 3, 59-66; Frontiers in phanyl, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, Bioscience (2009) 14, 2657-2665). Accordingly, there is a haloalkylsulphonyl, alkylcarbonyl, alkoxycarbonyl and/or need for further insecticides and/or parasiticides. cycloalkyl, cycloalkyl which is optionally monosubstituted The pyrazin-2-ylpyrazoles of the formula (I) given below 30 or independently polysubstituted by alkyl, haloalkyl and/or are described in the parallel pending application PCT/ halogen; haloalkyl which is optionally monosubstituted or EP2010/003060 (WO 2010/136145). independently polysubstituted by alkoxy, alkylsulphanyl, Accordingly, it is an object of the present invention to haloalkylsulphanyl, alkylsulphinyl, haloalkylsulphinyl, provide alternative insecticidal and/or parasiticidal products alkylsulphonyl, haloalkylsulphonyl and/or phenyl which is having, compared to the active compounds known from the 35 optionally monosubstituted or independently polysubstituted prior art, improved activity and/or a broader activity spec by halogen, alkyl, haloalkyl and/or alkoxy, phenyl which is trum, in particular in activity-enhancing combination with optionally monosubstituted or independently polysubstituted other ectoparasiticides and/or synergists known in the field of by halogen, alkyl, haloalkyl and/or alkoxy; benzyl which is Veterinary medicine. optionally monosubstituted or independently polysubstituted The active compounds referred to in the present description 40 by halogen, alkyl, haloalkyl and/or alkoxy; cyano, formyl. by their common name are known, for example, from “The alkylcarbonyl, CH-NO H. —CH=NO-alkyl, Pesticide Manual” 14th Ed., British Crop Protection Council -CH=NO-haloalkyl, -C(CH)—NO H. —C(CH)= 2006, and the website http://www.alanwood.net/pesticides. NO-alkyl or —C(CH)—NO-haloalkyl, It has now been found that active compound combinations R represents optionally substituted amino, where amino comprising, as component A, certain pyrazin-2-ylpyrazoles 45 may be monosubstituted or independently disubstituted by and, as component B, a furtherectoparasiticidally active com alkyl, haloalkyl, alkoxyalkyl, alkylsulphanylalkyl, alkylsul pound, have very good ectoparasiticidal activities of Veteri phinylalkyl, alkylsulphonylalkyl, alkylcarbonyl, cycloalkyl, nary relevance. cycloalkylalkyl, alkenyl, where the radicals listed above are Accordingly, the invention relates to products comprising, optionally Substituted by halogen, cyano, alkoxy, alkoxycar as component A, a compound of the general formula (I) 50 bonyl and phenyl, where the phenyl ring is optionally mono or polysubstituted by one or more substituents independently of one another selected from the group consisting of halogen, alkyl, haloalkyl and alkoxy; alkynyl, alkoxycarbonyl, alkeny (I) loxycarbonyl, alkinyloxycarbonyl, alkoxycarbonylalkyl, 55 alkoxycarbonylcarbonyl, heterocyclyl, heteroaryl, heterocy clylalkyl or heteroarylalkyl, where the heterocyclic or het eroaromatic ring may optionally be mono- or poly Substituted by one or more Substituents independently
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